Trifluoroacetic acid → [7-(2-Amino-ethoxy)-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl]-acetic Acid Methyl Ester Trifluoroacetate

HRID 2301970Notes

Reaction equation

HRID 2301970 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][C:10]([O:15][CH2:16][CH2:17][NH:18]C(OC(C)(C)C)=O)=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:26].[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31]>C(Cl)Cl>[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31].[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][C:10]([O:15][CH2:16][CH2:17][NH2:18])=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18462590[7-(2-Tert-butoxycarbonylamino-ethoxy)-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl]acetic acid methyl ester

Product 1

HCID 69979259[7-(2-Amino-ethoxy)-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl]-acetic Acid Methyl Ester TrifluoroacetateYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[7-(2-tert-Butoxycarbonylamino-ethoxy)-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl]-acetic acid methyl ester (2.5 g, 6.6 mmol) and trifluoroacetic acid (5.1 mL, 66 mmol) were combined in methylene chloride (25 mL) at 25° C. After 18 h, the solution was concentrated in vacuo to give the title compound as a tan solid (2.6 g).

Workup

  1. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-d6882a1e07a54cd09c325882a255b463
Source dataset
uspto-grants-2002_08
Patent number
US06429214B1

Reaction notes

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